The Ultimate Challenge!!!

[union_jak]

Updated to 2011...

The Peacemaker - George Clooney, Nicole Kidman
One Fine Day - George Clooney, Michelle Pfeiffer
My Life - Michael Keaton, Nicole Kidman
Man on the Moon - Jim Carrey, Danny DeVito, Vincent Schiavelli
Hoffa - Jack Nicholson, Danny DeVito
One Flew Over The Cuckoo's Nest - Jack Nicholson, Danny DeVito, Vincent Schiavelli
Wolf - Jack Nicholson, Michelle Pfeiffer
The Pledge - Jack Nicholson, Aaron Eckhart
Se7en - Morgan Freeman, Mark Boone Junior
The Prestige - Christian Bale, Michael Caine
Quicksand - Michael Keaton, Michael Caine
Sleepy Hollow - Christopher Walken, Michael Gough
First Daughter - Katie Holmes, Michael Keaton
Bewitched - Nicole Kidman, Michael Caine
Twins - Arnold Shwarzennegger, Danny DeVito
Thank You For Smoking - Aaron Eckhart, Katie Holmes
Out of Sight - George Clooney, Michael Keaton
The Bucket List - Jack Nicholson, Morgan Freeman
Equilibrium - Christian Bale & William Fichtner
The Age of Innocence - Michael Gough & Michelle Pfeiffer
Live From Baghdad - Michael Keaton & Michael Murphy
Death to Smoochy - Danny DeVito & Tracey Walter, Vincent Schiavelli
The Patriot - Heath Ledger & Tom Wilkinson
The Witches of Eastwick - Jack Nicholson, Michelle Pfeiffer
Johnny Dangerously - Michael Keaton, Danny DeVito
Top Secret! - Val Kilmer, Michael Gough
Donnie Darko - Maggie Gyllenhaal & Drew Barrymore
Clean & Sober - Michael Keaton & Morgan Freeman
Cobb - Tommy Lee Jones & Robert Wuhl
True Romance Gary Oldman, Christopher Walken, Val Kilmer
JFK Tommy Lee Jones, Gary Oldman
Paycheck Uma Thurman, Aaron Eckhart
The Prince of Egypt Michelle Pfeiffer, Val Kilmer
Girl With a Pearl Earring Tom Wilkinson, Cillian Murphy
Henry & June Gary Oldman, Uma Thurman
Kinsey Liam Neeson, Chris O'Donnell
Mad Love Drew Barrymoore Chris O'Donnell
Blast From The Past Christopher Walken, Alicia Silverstone
Excess Baggage Christopher Walken, Alicia Silverstone
A Midsummer Night's Dream Michelle Pfeiffer, Christian Bale
Goldmember Michael Caine, Danny DeVito
Junior Arnold Schwartenegger, Danny DeVito
LA Confidential Kim Basinger, Danny DeVito
Mars Attacks! Jack Nicholson, Danny DeVito
Pulp Fiction Christopher Walken, Uma Thurman
Wayne's World 2 Kim Basinger, Drew Barrymoore, Christopher Walken
Les Miserables Liam Neeson, Uma Thurman
Dangerous Liasons Uma Thurman, Michelle Pfeiffer
Eternal Sunshine of the Spotless Mind Jim Carrey,Tom Wilkinson
Cold Mountain Nicole Kidman, Cillian Murphy
Bruce Almighty Morgan Freeman, Jim Carrey
Heat- Val Kilmer, William Fitchner
Desperate Measures- Michael Keaton, Tracey Walter
Momento - Mark Boone Jnr., Larry Holden
Prophecy II - Christopher Walken, Eric Roberts
Predator- Arnold Schwarzenegger, Jesse Ventura
The Running Man- Arnold Schwarzenegger, Jesse Ventura
Shaft- Pat Hingle, Christian Bale
Breakfast on Pluto- Liam Neeson, Cilian Murphy
The Cable Guy- Jim Carrey, Eric Roberts
The Missing- Aaron Eckhart, Val Kilmer, Tommy Lee Jones
The Perfect Storm- George Clooney, William Fichtner
Be Cool- Danny DeVito, Uma Thurman
Ladyhawke - Rutger Hauer & Michelle Pfeiffer
Nighthawks - Rutger Hauer & Billy Dee Williams
Johnny Be Good - Anthony Michael Hall & Uma Thurman
Get Carter remake - Michael Caine & Mark Boone Jr
The Dead Pool - Liam Neeson & Jim Carrey
Hairspray- Michelle Pfeiffer, Christopher Walken
The Company- Michael Keaton, Chris O'Donnell
Reign of Fire- Christian Bale, Jack Gleeson
The Stepford Wives remake- Nicole Kidman, Christopher Walken
Kill Bill- Uma Thurman, Vivica A. Fox, Michael Jai White
Michael Clayton - George Clooney, Tom Wilkinson
Go- Katie Holmes, William Fichtner
Thank You For Smoking- Katie Holmes, Aaron Eckhart
The Lonely Maiden- Morgan Freeman, Christopher Walken
The Dirt- Christopher Walken, Val Kilmer
Nurse Betty - Morgan Freeman, Aaron Eckhart
Meteor Man - Frank Gorshin, Tommy "Zeus" Lister
Blue Sky - Tommy Lee Jones, Chris O'Donnell
Shawshank Redeption- Morgan Freeman, Clancy Brown
Conan The Destroyer - Arnold Schwarzenegger and Tracey Walter
Inception - Ken Watanabe, Cillian Murphy, Michael Caine, Tom Hardy
Alice In Wonderland - Anne Hathaway, Michael Gough
Brokeback Mountain - Anne Hathaway, Heath Ledger
Ella Enchanted - Anne Hathaway, Vivica A. Fox
Black Hawk Down - Tom Hardy, William Fichtner
The Code - Morgan Freeman, Tom Hardy
Tinker, Tailor, Soldier, Spy - Tom Hardy, Gary Oldman

 

[Two-Face]

Rabbit Hole - Nicole Kidman, Aaron Eckhart
The Real McCoy - Val Kilmer, Kim Basinger

 

[union_jak]

Oooh good ones

 

[BruceWanner]

tom cruise... and he was banging katie holmes, so i guess thats close enough for that guy

Don't forget that Cruise was also with Nicole Kidman for most of the 90's. That's both Rachel Dawes and Chase Meridian.

 

[BruceWanner]

Shawshank Redeption- Morgan Freeman and Clancy Brown. Brown played a guard in Batman & Robin. He also voices Lex Luthor in the DCAU(Justice League, etc), voiced Mr. Freeze in The Batman animated series, AND voiced characters in Batman Beyond and The Brave and The Bold.

Sorry, but Clancy Brown was not the guard in Batman and Robin, unless I missed it. If you're thinking of the eye patched Arkham guard with Jesse Ventura, that was Ralf Moeller. Also, Brown didn't voice Mr. Freeze in Batman: The Animated Series or Batman Beyond. In both of those series, Michael Ansara voiced Freeze.

 

[Sky Captain]

He didn't mean Batman THE Animated Series, he meant THE Batman cartoon, where Brown did voice the incarnation of that Freeze.

 

[BruceWanner]

He didn't mean Batman THE Animated Series, he meant THE Batman cartoon, where Brown did voice the incarnation of that Freeze.

I apologize then.

 

[ALP]

Yeah the only thing I was wrong about was him in B&R. You're right. The guy playing the guard just looked like him, I confused the two. He was Mr Freeze AND Bane in "The Batman," Per Degaton in "Batman Brave and the Bold," and Big Time in "Batman Beyond."